Electronic circular dichroism behavior of chiral Phthiobuzone
Phthiobuzone is a bis(thiosemicarbazone) derivative with a single chiral center which has been used as a racemate in the clinical treatment of herpes and trachoma diseases. In this study, its two enantiomers were prepared from chiral amino acids and their absolute configurations were investigated by...
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Elsevier
2014
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| Online Access: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4590302/ |
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pubmed-45903022015-11-17 Electronic circular dichroism behavior of chiral Phthiobuzone Li, Li Wang, Lin Si, Yikang Short Communication Phthiobuzone is a bis(thiosemicarbazone) derivative with a single chiral center which has been used as a racemate in the clinical treatment of herpes and trachoma diseases. In this study, its two enantiomers were prepared from chiral amino acids and their absolute configurations were investigated by electronic circular dichroism (ECD) combined with modern quantum-chemical calculations using time-dependent density functional theory. It was found that solvation changed both the conformational distribution and the ECD spectrum of each conformer. The theoretical ECD spectra of the two enantiomers were in good agreement with the experimentally determined spectra of the corresponding isomers in dimethyl sulfoxide. The ECD behavior of the bis(thiosemicarbazone) chromophore in a chiral environment is also discussed. Our results indicate that ECD spectroscopy may be a useful tool for the stereochemical evaluation of chiral drugs. Elsevier 2014-04 2014-02-26 /pmc/articles/PMC4590302/ /pubmed/26579380 http://dx.doi.org/10.1016/j.apsb.2014.01.001 Text en © 2014 Chinese Pharmaceutical Association and Institute of Materia Medica, Chinese Academy of Medical Sciences. Production and hosting by Elsevier B.V. http://creativecommons.org/licenses/by-nc-nd/3.0/ Open access under CC BY-NC-ND license.(http://creativecommons.org/licenses/by-nc-nd/3.0/). |
| repository_type |
Open Access Journal |
| institution_category |
Foreign Institution |
| institution |
US National Center for Biotechnology Information |
| building |
NCBI PubMed |
| collection |
Online Access |
| language |
English |
| format |
Online |
| author |
Li, Li Wang, Lin Si, Yikang |
| spellingShingle |
Li, Li Wang, Lin Si, Yikang Electronic circular dichroism behavior of chiral Phthiobuzone |
| author_facet |
Li, Li Wang, Lin Si, Yikang |
| author_sort |
Li, Li |
| title |
Electronic circular dichroism behavior of chiral Phthiobuzone |
| title_short |
Electronic circular dichroism behavior of chiral Phthiobuzone |
| title_full |
Electronic circular dichroism behavior of chiral Phthiobuzone |
| title_fullStr |
Electronic circular dichroism behavior of chiral Phthiobuzone |
| title_full_unstemmed |
Electronic circular dichroism behavior of chiral Phthiobuzone |
| title_sort |
electronic circular dichroism behavior of chiral phthiobuzone |
| description |
Phthiobuzone is a bis(thiosemicarbazone) derivative with a single chiral center which has been used as a racemate in the clinical treatment of herpes and trachoma diseases. In this study, its two enantiomers were prepared from chiral amino acids and their absolute configurations were investigated by electronic circular dichroism (ECD) combined with modern quantum-chemical calculations using time-dependent density functional theory. It was found that solvation changed both the conformational distribution and the ECD spectrum of each conformer. The theoretical ECD spectra of the two enantiomers were in good agreement with the experimentally determined spectra of the corresponding isomers in dimethyl sulfoxide. The ECD behavior of the bis(thiosemicarbazone) chromophore in a chiral environment is also discussed. Our results indicate that ECD spectroscopy may be a useful tool for the stereochemical evaluation of chiral drugs. |
| publisher |
Elsevier |
| publishDate |
2014 |
| url |
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4590302/ |
| _version_ |
1613482535168245760 |